Mendoza 1 Nikko Mendoza 57071054 Chem 51LB Preparation of a Synthetic Plant Hormone The purpose of this lab was

to scale a piece of chemistry procedure literature in a way that could be carried out in the lab. Also, 4-chlorophenoxyacetic acid was synthesized from chloroacetic acid and 1 M sodium 4-chlorophenolate-2.5 M sodium hydroxide solution through and SN2 reaction. The SN2 reaction stands for substitution, nucleophilic, bimolecular reaction. In this reaction, a nucleophile attacks the back of a substrate and displaces the leaving group on the substrate. For SN2 to occur, a good nucleophile and a good leaving group must be present. Also if the reaction involves a primary carbon, a SN2 reaction is favored. The 4-chlorophenol is going to act as a nucleophile, but first it needs to be deprotonated by sodium hydroxide in order to do so. The chloroacetic acid will act an electrophile. The hydroxyl group in the acid will also be deprotonated by sodium hydroxide because it is the most acidic proton in solution. Once 4chlorophenol has been deprotonated by the sodium hydroxide base, it will attack the electrolphilic chloroacetic acid, and cause the chlorine to become the leaving group. In one step, the 4-chlorophenol substitutes the chlorine in the chloroacetic acid and 4-chlorophenoxyacetic acid is synthesized.

Results: The product was a solid that was white and crystallized powder. Percent Yield Percent Recovery Melting Point Range (Degrees Celsius)

Mendoza 2 30.4% 28% 156-158

After the synthesis reaction, 0.112 grams of product was created. The product looked like white crystals. The weight of the starting product was 0.187 grams. The theoretical yield of the synthesis came out to be 0.369 grams. Dividing the theoretical yield by the actual yield gave the percent yield of 30.4%. After recrystallization of the product, 0.031 grams remained equating to a 28% recovery. The low percent recovery can be attributed to using too much solvent. It was necessary to evaporate some of the solvent and some of the product may have been lost that way. After a melting point test, the products melting range was found to be 156 degrees Celsius to 158 degrees Celsius. The literal melting point of 4-chloropheoxyacetic acid is 156-157 degrees Celsius. It can be assumed that the synthesis was carried out properly. The product can also be assumed to be pure because the entire product was not recovered after the recrystallization, meaning that impurities were taken out of the crystal lattice. There was an error in adding to much solvent during the recrystallization portion and that caused a low percent recovery because the excess solvent needed to be evaporated in order for the precipitate to recrystallize. A low percent yield can be attributed to some other molecules such as the chloroacetic acid acting as a nucleophile and going through a different reaction pathway and thus creating other byproducts that do not precipitate. Chromatography can be a good way in which to identify a substance as well as checking its purity. For future experiments, to get a better yield, conditions that would favor 4-chlorophenol to be the only nucleophile would have to be used.